Lithium diisobutylaluminum hydride → [3-Chloro-2-(propan-2-yloxy)phenyl]methanol

Diisobutylaluminum lithium hydride (26.8 mL of a 1.0 M in hexanes, 26.8 mmol) was added dropwise to a solution of 3-chloro-2-isopropoxybenzoic acid isopropyl ester (2.29 g, 8.94 mmol) in THF (20 mL) under N2 at 0° C. After the addition was complete, the ice bath was removed, the solution warmed to ambient temperature, and the reaction mixture stirred for 5 d. The reaction was cooled to 0° C. and quenched using 1N HCl (100 mL) until all the solids dissolved. The solution was extracted with Et2O (3×50 mL). The combined organics were washed with brine (2×100 mL), dried (Na2SO4) and concentrated to yield the title compound (1.60 g, 89%) as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 7.41 (d, J=4.5 Hz, 1H), 7.33 (dd, J=8.0, 1.5 Hz, 1H), 7.11 (t, J=8.0 Hz, 1H), 5.19 (t, J=5.7 Hz, 1H), 4.53 (d, J=5.5 Hz, 1H), 4.44-4.36 (m, 1H), 1.24 (d, J=6.1 Hz, 6H).

1. additionAfter the addition
2. customthe ice bath was removed
3. temperatureThe reaction was cooled to 0° C.
4. customquenched
5. dissolutiondissolved
6. extractionThe solution was extracted with Et2O (3×50 mL)
7. washThe combined organics were washed with brine (2×100 mL)
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated

ORD record

ord-79e7cd1270fe424ba5004868a5e3fee4

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879872B2